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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2021-09-14 15:20:01 UTC

HMDB ID

HMDB0000265

Secondary Accession Numbers

HMDB0006780
HMDB00265
HMDB06780

Metabolite Identification

Common Name

Liothyronine

Description

Liothyronine is a T3 thyroid hormone normally synthesized and secreted by the thyroid gland in much smaller quantities than thyroxine (T4). Most T3 is derived from peripheral monodeiodination of T4 at the 5' position of the outer ring of the iodothyronine nucleus. The hormone that is finally delivered and used by the tissues is mainly T3. Liothyronine is mildly toxic by ingestion and is an experimental teratogen. When heated to decomposition it emits toxic fumes of NOx, I(-), and Cl(-) (Sax's Dangerous Properties of Industrial Materials).

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0000265
     RDKit          3D
Liothyronine
 35 36  0  0  0  0  0  0  0  0999 V2000
    4.1888    0.7831   -0.2732 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1775   -0.6176    0.1513 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9616   -1.2546   -0.4790 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7146   -0.6075   -0.0608 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0319   -1.0418    1.0526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1353   -0.4104    1.4153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1864   -1.0580    3.1057 I   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6384    0.6431    0.6955 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7986    1.2987    1.0247 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0496    0.9316    0.5540 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1695   -0.1353   -0.2841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4439   -0.4783   -0.7397 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5449    0.2514   -0.3448 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8336   -0.0445   -0.7664 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4284    1.3482    0.5158 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1214    2.4458    1.1042 I   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1522    1.6575    0.9458 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0471    1.0843   -0.4281 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6686    2.6977   -1.5806 I   0  0  0  0  0  0  0  0  0  0  0  0
    1.2095    0.4484   -0.7814 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3799   -1.2806   -0.4226 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5871   -2.5027   -0.1915 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2967   -0.6034   -1.2124 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7864    1.3668    0.3424 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4592    0.8263   -1.2754 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1437   -0.7131    1.2390 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9892   -2.3389   -0.2011 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0328   -1.2191   -1.5838 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3856   -1.8716    1.6586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3128   -0.6940   -0.5844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5954   -1.3112   -1.4026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0560   -0.8069   -1.3859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0463    2.5077    1.6152 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7478    0.7938   -1.6626 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0417   -0.0950   -0.7451 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  6  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 15 17  2  0
  8 18  1  0
 18 19  1  0
 18 20  2  0
  2 21  1  0
 21 22  2  0
 21 23  1  0
 20  4  1  0
 17 10  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  1
  3 27  1  0
  3 28  1  0
  5 29  1  0
 11 30  1  0
 12 31  1  0
 14 32  1  0
 17 33  1  0
 20 34  1  0
 23 35  1  0
M  END

  Mrv1652311121923412D          

 23 24  0  0  0  0            999 V2000
10001.806310001.5689    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.378310002.3928    0.0000 I   0  0  0  0  0  0  0  0  0  0  0  0
10001.8063 9999.9209    0.0000 I   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9511 9999.9209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.237510000.3339    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9997.5239 9999.9209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.810310000.3339    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.5239 9999.0969    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.237510001.1568    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10003.2339 9999.0969    0.0000 I   0  0  0  0  0  0  0  0  0  0  0  0
10004.6594 9999.9209    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.092610001.1577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.378210001.5703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.663610001.1576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.663510000.3327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.3781 9999.9202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.092710000.3327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.947810001.1577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.233310001.5703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.518610001.1576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.518610000.3327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.2331 9999.9202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.947810000.3327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  9  1  1  0  0  0
  6  7  1  0  0  0  0
  6  8  2  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 12  1  0  0  0  0
  1 12  1  0  0  0  0
 13  2  1  0  0  0  0
 15  4  1  0  0  0  0
 17  3  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 18  1  0  0  0  0
  1 20  1  0  0  0  0
 22 10  1  0  0  0  0
 23 11  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0000265

> <DATABASE_NAME>
hmdb

> <SMILES>
N[C@@H](CC1=CC(I)=C(OC2=CC(I)=C(O)C=C2)C(I)=C1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C15H12I3NO4/c16-9-6-8(1-2-13(9)20)23-14-10(17)3-7(4-11(14)18)5-12(19)15(21)22/h1-4,6,12,20H,5,19H2,(H,21,22)/t12-/m0/s1

> <INCHI_KEY>
AUYYCJSJGJYCDS-LBPRGKRZSA-N

> <FORMULA>
C15H12I3NO4

> <MOLECULAR_WEIGHT>
650.9735

> <EXACT_MASS>
650.790038137

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
35

> <JCHEM_AVERAGE_POLARIZABILITY>
43.92059819460361

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-amino-3-[4-(4-hydroxy-3-iodophenoxy)-3,5-diiodophenyl]propanoic acid

> <ALOGPS_LOGP>
0.82

> <JCHEM_LOGP>
2.798504958851472

> <ALOGPS_LOGS>
-4.52

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.49112819466963

> <JCHEM_PKA_STRONGEST_ACIDIC>
0.3025527340740366

> <JCHEM_PKA_STRONGEST_BASIC>
9.48230448922794

> <JCHEM_POLAR_SURFACE_AREA>
92.78

> <JCHEM_REFRACTIVITY>
113.42549999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.95e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
liothyronine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0000265
     RDKit          3D
Liothyronine
 35 36  0  0  0  0  0  0  0  0999 V2000
    4.1888    0.7831   -0.2732 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1775   -0.6176    0.1513 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9616   -1.2546   -0.4790 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7146   -0.6075   -0.0608 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0319   -1.0418    1.0526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1353   -0.4104    1.4153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1864   -1.0580    3.1057 I   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6384    0.6431    0.6955 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7986    1.2987    1.0247 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0496    0.9316    0.5540 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1695   -0.1353   -0.2841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4439   -0.4783   -0.7397 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5449    0.2514   -0.3448 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8336   -0.0445   -0.7664 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4284    1.3482    0.5158 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1214    2.4458    1.1042 I   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1522    1.6575    0.9458 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0471    1.0843   -0.4281 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6686    2.6977   -1.5806 I   0  0  0  0  0  0  0  0  0  0  0  0
    1.2095    0.4484   -0.7814 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3799   -1.2806   -0.4226 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5871   -2.5027   -0.1915 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2967   -0.6034   -1.2124 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7864    1.3668    0.3424 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4592    0.8263   -1.2754 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1437   -0.7131    1.2390 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9892   -2.3389   -0.2011 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0328   -1.2191   -1.5838 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3856   -1.8716    1.6586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3128   -0.6940   -0.5844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5954   -1.3112   -1.4026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0560   -0.8069   -1.3859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0463    2.5077    1.6152 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7478    0.7938   -1.6626 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0417   -0.0950   -0.7451 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  6  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 15 17  2  0
  8 18  1  0
 18 19  1  0
 18 20  2  0
  2 21  1  0
 21 22  2  0
 21 23  1  0
 20  4  1  0
 17 10  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  1
  3 27  1  0
  3 28  1  0
  5 29  1  0
 11 30  1  0
 12 31  1  0
 14 32  1  0
 17 33  1  0
 20 34  1  0
 23 35  1  0
M  END

HEADER    PROTEIN                                 12-NOV-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-NOV-19         0                                  
HETATM    1  O   UNK     0    8670.0388669.595   0.000  0.00  0.00           O+0
HETATM    2  I   UNK     0    8667.3738671.133   0.000  0.00  0.00           I+0
HETATM    3  I   UNK     0    8670.0388666.519   0.000  0.00  0.00           I+0
HETATM    4  C   UNK     0    8664.7098666.519   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8663.3778667.290   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8662.0458666.519   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0    8660.7138667.290   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0    8662.0458664.981   0.000  0.00  0.00           O+0
HETATM    9  N   UNK     0    8663.3778668.826   0.000  0.00  0.00           N+0
HETATM   10  I   UNK     0    8672.7038664.981   0.000  0.00  0.00           I+0
HETATM   11  O   UNK     0    8675.3648666.519   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0    8668.7068668.828   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8667.3738669.598   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8666.0398668.828   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8666.0398667.288   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8667.3728666.518   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8668.7068667.288   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8674.0368668.828   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8672.7028669.598   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8671.3688668.828   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8671.3688667.288   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8672.7028666.518   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0    8674.0368667.288   0.000  0.00  0.00           C+0
CONECT    1   12   20                                                       
CONECT    2   13                                                            
CONECT    3   17                                                            
CONECT    4    5   15                                                       
CONECT    5    4    6    9                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9    5                                                            
CONECT   10   22                                                            
CONECT   11   23                                                            
CONECT   12   13   17    1                                                  
CONECT   13   12   14    2                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16    4                                                  
CONECT   16   15   17                                                       
CONECT   17   16   12    3                                                  
CONECT   18   19   23                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21    1                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   10                                                  
CONECT   23   22   18   11                                                  
MASTER        0    0    0    0    0    0    0    0   23    0   48    0
END

COMPND    HMDB0000265
HETATM    1  N1  UNL     1       4.189   0.783  -0.273  1.00  0.00           N  
HETATM    2  C1  UNL     1       4.178  -0.618   0.151  1.00  0.00           C  
HETATM    3  C2  UNL     1       2.962  -1.255  -0.479  1.00  0.00           C  
HETATM    4  C3  UNL     1       1.715  -0.607  -0.061  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.032  -1.042   1.053  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.135  -0.410   1.415  1.00  0.00           C  
HETATM    7  I1  UNL     1      -1.186  -1.058   3.106  1.00  0.00           I  
HETATM    8  C6  UNL     1      -0.638   0.643   0.696  1.00  0.00           C  
HETATM    9  O1  UNL     1      -1.799   1.299   1.025  1.00  0.00           O  
HETATM   10  C7  UNL     1      -3.050   0.932   0.554  1.00  0.00           C  
HETATM   11  C8  UNL     1      -3.169  -0.135  -0.284  1.00  0.00           C  
HETATM   12  C9  UNL     1      -4.444  -0.478  -0.740  1.00  0.00           C  
HETATM   13  C10 UNL     1      -5.545   0.251  -0.345  1.00  0.00           C  
HETATM   14  O2  UNL     1      -6.834  -0.044  -0.766  1.00  0.00           O  
HETATM   15  C11 UNL     1      -5.428   1.348   0.516  1.00  0.00           C  
HETATM   16  I2  UNL     1      -7.121   2.446   1.104  1.00  0.00           I  
HETATM   17  C12 UNL     1      -4.152   1.657   0.946  1.00  0.00           C  
HETATM   18  C13 UNL     1       0.047   1.084  -0.428  1.00  0.00           C  
HETATM   19  I3  UNL     1      -0.669   2.698  -1.581  1.00  0.00           I  
HETATM   20  C14 UNL     1       1.209   0.448  -0.781  1.00  0.00           C  
HETATM   21  C15 UNL     1       5.380  -1.281  -0.423  1.00  0.00           C  
HETATM   22  O3  UNL     1       5.587  -2.503  -0.192  1.00  0.00           O  
HETATM   23  O4  UNL     1       6.297  -0.603  -1.212  1.00  0.00           O  
HETATM   24  H1  UNL     1       4.786   1.367   0.342  1.00  0.00           H  
HETATM   25  H2  UNL     1       4.459   0.826  -1.275  1.00  0.00           H  
HETATM   26  H3  UNL     1       4.144  -0.713   1.239  1.00  0.00           H  
HETATM   27  H4  UNL     1       2.989  -2.339  -0.201  1.00  0.00           H  
HETATM   28  H5  UNL     1       3.033  -1.219  -1.584  1.00  0.00           H  
HETATM   29  H6  UNL     1       1.386  -1.872   1.659  1.00  0.00           H  
HETATM   30  H7  UNL     1      -2.313  -0.694  -0.584  1.00  0.00           H  
HETATM   31  H8  UNL     1      -4.595  -1.311  -1.403  1.00  0.00           H  
HETATM   32  H9  UNL     1      -7.056  -0.807  -1.386  1.00  0.00           H  
HETATM   33  H10 UNL     1      -4.046   2.508   1.615  1.00  0.00           H  
HETATM   34  H11 UNL     1       1.748   0.794  -1.663  1.00  0.00           H  
HETATM   35  H12 UNL     1       7.042  -0.095  -0.745  1.00  0.00           H  
CONECT    1    2   24   25
CONECT    2    3   21   26
CONECT    3    4   27   28
CONECT    4    5    5   20
CONECT    5    6   29
CONECT    6    7    8    8
CONECT    8    9   18
CONECT    9   10
CONECT   10   11   11   17
CONECT   11   12   30
CONECT   12   13   13   31
CONECT   13   14   15
CONECT   14   32
CONECT   15   16   17   17
CONECT   17   33
CONECT   18   19   20   20
CONECT   20   34
CONECT   21   22   22   23
CONECT   23   35
END

HMDB0000265
     RDKit          3D
Liothyronine
 35 36  0  0  0  0  0  0  0  0999 V2000
    4.1888    0.7831   -0.2732 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1775   -0.6176    0.1513 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9616   -1.2546   -0.4790 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7146   -0.6075   -0.0608 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0319   -1.0418    1.0526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1353   -0.4104    1.4153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1864   -1.0580    3.1057 I   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6384    0.6431    0.6955 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7986    1.2987    1.0247 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0496    0.9316    0.5540 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1695   -0.1353   -0.2841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4439   -0.4783   -0.7397 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5449    0.2514   -0.3448 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8336   -0.0445   -0.7664 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4284    1.3482    0.5158 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1214    2.4458    1.1042 I   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1522    1.6575    0.9458 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0471    1.0843   -0.4281 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6686    2.6977   -1.5806 I   0  0  0  0  0  0  0  0  0  0  0  0
    1.2095    0.4484   -0.7814 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3799   -1.2806   -0.4226 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5871   -2.5027   -0.1915 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2967   -0.6034   -1.2124 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7864    1.3668    0.3424 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4592    0.8263   -1.2754 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1437   -0.7131    1.2390 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9892   -2.3389   -0.2011 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0328   -1.2191   -1.5838 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3856   -1.8716    1.6586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3128   -0.6940   -0.5844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5954   -1.3112   -1.4026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0560   -0.8069   -1.3859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0463    2.5077    1.6152 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7478    0.7938   -1.6626 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0417   -0.0950   -0.7451 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  6  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 15 17  2  0
  8 18  1  0
 18 19  1  0
 18 20  2  0
  2 21  1  0
 21 22  2  0
 21 23  1  0
 20  4  1  0
 17 10  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  1
  3 27  1  0
  3 28  1  0
  5 29  1  0
 11 30  1  0
 12 31  1  0
 14 32  1  0
 17 33  1  0
 20 34  1  0
 23 35  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3,5,3'-Triiodo-L-thyronine	ChEBI
3,5,3'-Triiodothyronine	ChEBI
3,5,3'TRIIODOTHYRONINE	ChEBI
4-(4-Hydroxy-3-iodophenoxy)-3,5-diiodo-L-phenylalanine	ChEBI
L-3,5,3'-Triiodothyronine	ChEBI
L-T3	ChEBI
Liothyroninum	ChEBI
Liotironina	ChEBI
O-(4-Hydroxy-3-iodophenyl)-3,5-diiodo-L-tyrosine	ChEBI
T3	ChEBI
Tertroxin	ChEBI
Tresitope	ChEBI
Triiodothyronine	ChEBI
3,3',5-Triiodo-L-thyronine	Kegg
Thyrolar	Kegg
3,3',5-Triiodothyronine	HMDB
Cytomel	HMDB
T3 Thyroid hormone	HMDB
Thyroid hormone, T3	HMDB
Liothyronine sodium	HMDB
3,3',5'-Triiodo-L-thyronine	HMDB
3,3',5'-Triiodothyronine	HMDB
4-(4-Hydroxy-3-iodophenoxy)-3,5-diiodophenylalanine	HMDB
Cyronine	HMDB
L-3,3',5-Triiodo-thyronine	HMDB
L-3,3',5-Triiodothyronine	HMDB
L-3-[4-(4-Hydroxy-3-iodophenoxy)-3,5-diiodophenyl]-alanine	HMDB
L-Liothyronine	HMDB
L-Triiodothyronine	HMDB
Liothyronin	HMDB
Triiodo-L-thyronine	HMDB

Chemical Formula

C₁₅H₁₂I₃NO₄

Average Molecular Weight

650.9735

Monoisotopic Molecular Weight

650.790038137

IUPAC Name

(2S)-2-amino-3-[4-(4-hydroxy-3-iodophenoxy)-3,5-diiodophenyl]propanoic acid

Traditional Name

liothyronine

CAS Registry Number

6893-02-3

SMILES

N[C@@H](CC1=CC(I)=C(OC2=CC(I)=C(O)C=C2)C(I)=C1)C(O)=O

InChI Identifier

InChI=1S/C15H12I3NO4/c16-9-6-8(1-2-13(9)20)23-14-10(17)3-7(4-11(14)18)5-12(19)15(21)22/h1-4,6,12,20H,5,19H2,(H,21,22)/t12-/m0/s1

InChI Key

AUYYCJSJGJYCDS-LBPRGKRZSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylalanine and derivatives. Phenylalanine and derivatives are compounds containing phenylalanine or a derivative thereof resulting from reaction of phenylalanine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Phenylalanine and derivatives

Alternative Parents

Substituents

Phenylalanine or derivatives
Diphenylether
Diaryl ether
3-phenylpropanoic-acid
Alpha-amino acid
Amphetamine or derivatives
L-alpha-amino acid
Phenoxy compound
2-iodophenol
2-halophenol
Phenol ether
Iodobenzene
1-hydroxy-2-unsubstituted benzenoid
Halobenzene
Phenol
Aralkylamine
Aryl iodide
Aryl halide
Monocyclic benzene moiety
Benzenoid
Amino acid
Ether
Carboxylic acid
Monocarboxylic acid or derivatives
Organic nitrogen compound
Primary aliphatic amine
Organohalogen compound
Organoiodide
Organonitrogen compound
Organooxygen compound
Primary amine
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Amine
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

iodothyronine (CHEBI:18258 )
iodophenol (CHEBI:18258 )
2-halophenol (CHEBI:18258 )
thyroxine (C02465 )
Other amino acids (C02465 )

Ontology

Not Available

Adipose tissue (HMDB: HMDB0000265)

Epithelium

Epidermis (HMDB: HMDB0000265)

Muscle tissue

Skeletal muscle (HMDB: HMDB0000265)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 10197568)
Saliva (PMID: 15179829)

Organ

Gland

Adrenal Gland (HMDB: HMDB0000265)
Thyroid gland (HMDB: HMDB0000265)

Cell

Hematocyte

Platelet (HMDB: HMDB0000265)

Excreta

Biofluid or Excreta

Urine (PMID: 7256725)

Cellular substructure

Source

Exogenous

Exogenous (HMDB: HMDB0000265)

Food

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Milk and milk product

Unfermented milk

Milk (Cow) (FooDB: FOOD00618)

Endogenous

Endogenous (HMDB: HMDB0000265)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Tyrosine Metabolism (HMDB: HMDB0000265)
Thyroid hormone synthesis (PathBank: SMP0087269)
Thyroid hormone synthesis (PathBank: SMP0063679)

Role

Industrial application

Pharmaceutical industry

Biomarker

Proprotein Convertase 1/3 Deficiency (MarkerDB: MDB00000128)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	MetCCS_train_pos	209.677	30932474
[M+H]+	Not Available	209.8	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000488

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.02 g/L	ALOGPS
logP	0.82	ALOGPS
logP	2.8	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	0.3	ChemAxon
pKa (Strongest Basic)	9.48	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	92.78 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	113.43 m³·mol⁻¹	ChemAxon
Polarizability	43.92 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
AllCCS	[M+H]+	203.723	32859911
AllCCS	[M-H]-	197.665	32859911
DeepCCS	[M+H]+	207.033	30932474
DeepCCS	[M+H]+	206.913	30932474
DeepCCS	[M-H]-	204.485	30932474
DeepCCS	[M-H]-	204.363	30932474
DeepCCS	[M-2H]-	238.782	30932474
DeepCCS	[M+Na]+	214.135	30932474
DeepCCS	[M-2H]-	238.152	30932474
DeepCCS	[M+Na]+	213.505	30932474
AllCCS	[M+H]+	203.7	32859911
AllCCS	[M+H-H2O]+	202.3	32859911
AllCCS	[M+NH4]+	205.0	32859911
AllCCS	[M+Na]+	205.3	32859911
AllCCS	[M-H]-	197.7	32859911
AllCCS	[M+Na-2H]-	199.4	32859911
AllCCS	[M+HCOO]-	201.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Liothyronine	N[C@@H](CC1=CC(I)=C(OC2=CC(I)=C(O)C=C2)C(I)=C1)C(O)=O	4675.4	Standard polar	33892256
Liothyronine	N[C@@H](CC1=CC(I)=C(OC2=CC(I)=C(O)C=C2)C(I)=C1)C(O)=O	3583.5	Standard non polar	33892256
Liothyronine	N[C@@H](CC1=CC(I)=C(OC2=CC(I)=C(O)C=C2)C(I)=C1)C(O)=O	3771.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Liothyronine,1TMS,isomer #1	C[Si](C)(C)OC1=CC=C(OC2=C(I)C=C(C[C@H](N)C(=O)O)C=C2I)C=C1I	3500.9	Semi standard non polar	33892256
Liothyronine,1TMS,isomer #2	C[Si](C)(C)OC(=O)[C@@H](N)CC1=CC(I)=C(OC2=CC=C(O)C(I)=C2)C(I)=C1	3505.5	Semi standard non polar	33892256
Liothyronine,1TMS,isomer #3	C[Si](C)(C)N[C@@H](CC1=CC(I)=C(OC2=CC=C(O)C(I)=C2)C(I)=C1)C(=O)O	3540.4	Semi standard non polar	33892256
Liothyronine,2TMS,isomer #1	C[Si](C)(C)OC(=O)[C@@H](N)CC1=CC(I)=C(OC2=CC=C(O[Si](C)(C)C)C(I)=C2)C(I)=C1	3520.6	Semi standard non polar	33892256
Liothyronine,2TMS,isomer #2	C[Si](C)(C)N[C@@H](CC1=CC(I)=C(OC2=CC=C(O[Si](C)(C)C)C(I)=C2)C(I)=C1)C(=O)O	3516.8	Semi standard non polar	33892256
Liothyronine,2TMS,isomer #3	C[Si](C)(C)N[C@@H](CC1=CC(I)=C(OC2=CC=C(O)C(I)=C2)C(I)=C1)C(=O)O[Si](C)(C)C	3485.2	Semi standard non polar	33892256
Liothyronine,2TMS,isomer #4	C[Si](C)(C)N([C@@H](CC1=CC(I)=C(OC2=CC=C(O)C(I)=C2)C(I)=C1)C(=O)O)[Si](C)(C)C	3627.2	Semi standard non polar	33892256
Liothyronine,3TMS,isomer #1	C[Si](C)(C)N[C@@H](CC1=CC(I)=C(OC2=CC=C(O[Si](C)(C)C)C(I)=C2)C(I)=C1)C(=O)O[Si](C)(C)C	3509.7	Semi standard non polar	33892256
Liothyronine,3TMS,isomer #1	C[Si](C)(C)N[C@@H](CC1=CC(I)=C(OC2=CC=C(O[Si](C)(C)C)C(I)=C2)C(I)=C1)C(=O)O[Si](C)(C)C	3176.4	Standard non polar	33892256
Liothyronine,3TMS,isomer #1	C[Si](C)(C)N[C@@H](CC1=CC(I)=C(OC2=CC=C(O[Si](C)(C)C)C(I)=C2)C(I)=C1)C(=O)O[Si](C)(C)C	3131.5	Standard polar	33892256
Liothyronine,3TMS,isomer #2	C[Si](C)(C)OC1=CC=C(OC2=C(I)C=C(C[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C=C2I)C=C1I	3638.7	Semi standard non polar	33892256
Liothyronine,3TMS,isomer #2	C[Si](C)(C)OC1=CC=C(OC2=C(I)C=C(C[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C=C2I)C=C1I	3317.3	Standard non polar	33892256
Liothyronine,3TMS,isomer #2	C[Si](C)(C)OC1=CC=C(OC2=C(I)C=C(C[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C=C2I)C=C1I	3305.8	Standard polar	33892256
Liothyronine,3TMS,isomer #3	C[Si](C)(C)OC(=O)[C@H](CC1=CC(I)=C(OC2=CC=C(O)C(I)=C2)C(I)=C1)N([Si](C)(C)C)[Si](C)(C)C	3610.9	Semi standard non polar	33892256
Liothyronine,3TMS,isomer #3	C[Si](C)(C)OC(=O)[C@H](CC1=CC(I)=C(OC2=CC=C(O)C(I)=C2)C(I)=C1)N([Si](C)(C)C)[Si](C)(C)C	3279.4	Standard non polar	33892256
Liothyronine,3TMS,isomer #3	C[Si](C)(C)OC(=O)[C@H](CC1=CC(I)=C(OC2=CC=C(O)C(I)=C2)C(I)=C1)N([Si](C)(C)C)[Si](C)(C)C	3301.0	Standard polar	33892256
Liothyronine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(OC2=C(I)C=C(C[C@H](N)C(=O)O)C=C2I)C=C1I	3786.6	Semi standard non polar	33892256
Liothyronine,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)[C@@H](N)CC1=CC(I)=C(OC2=CC=C(O)C(I)=C2)C(I)=C1	3777.3	Semi standard non polar	33892256
Liothyronine,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N[C@@H](CC1=CC(I)=C(OC2=CC=C(O)C(I)=C2)C(I)=C1)C(=O)O	3786.9	Semi standard non polar	33892256
Liothyronine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@@H](N)CC1=CC(I)=C(OC2=CC=C(O[Si](C)(C)C(C)(C)C)C(I)=C2)C(I)=C1	4009.3	Semi standard non polar	33892256
Liothyronine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N[C@@H](CC1=CC(I)=C(OC2=CC=C(O[Si](C)(C)C(C)(C)C)C(I)=C2)C(I)=C1)C(=O)O	4035.1	Semi standard non polar	33892256
Liothyronine,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N[C@@H](CC1=CC(I)=C(OC2=CC=C(O)C(I)=C2)C(I)=C1)C(=O)O[Si](C)(C)C(C)(C)C	3997.9	Semi standard non polar	33892256
Liothyronine,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N([C@@H](CC1=CC(I)=C(OC2=CC=C(O)C(I)=C2)C(I)=C1)C(=O)O)[Si](C)(C)C(C)(C)C	4071.1	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Liothyronine GC-MS (Non-derivatized) - 70eV, Positive	splash10-05a9-5090378000-014ef55558b58a3d38f2	2017-08-28	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Liothyronine GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-10-17	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Liothyronine GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-10-17	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Liothyronine GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-10-17	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Liothyronine GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-10-17	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Liothyronine GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-10-17	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Liothyronine GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-10-17	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Liothyronine GC-MS (TMS_2_4) - 70eV, Positive	Not Available	2021-10-17	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Liothyronine GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-10-17	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Liothyronine GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-10-17	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Liothyronine GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-10-17	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Liothyronine GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-10-17	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Liothyronine GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	2021-10-17	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Liothyronine GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	2021-10-17	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Liothyronine GC-MS (TBDMS_2_4) - 70eV, Positive	Not Available	2021-10-17	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Liothyronine GC-MS ("Liothyronine,1TMS,#1" TMS) - 70eV, Positive	Not Available	2021-11-02	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Liothyronine Quattro_QQQ 10V, N/A-QTOF (Annotated)	splash10-000i-0009001000-1d47041336da63b556e4	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Liothyronine Quattro_QQQ 25V, N/A-QTOF (Annotated)	splash10-000i-1009001000-15f70073b9018f013c9c	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Liothyronine Quattro_QQQ 40V, N/A-QTOF (Annotated)	splash10-000i-0009000000-71c231d7a3ab505815ff	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Liothyronine LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative-QTOF	splash10-0udi-0000009000-f932659d1e6d8a622985	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Liothyronine LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative-QTOF	splash10-0udi-0000009000-6506a7a71dab928abfb0	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Liothyronine LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative-QTOF	splash10-0fc0-0700119000-1df6db0e3031eb2739fa	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Liothyronine LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative-QTOF	splash10-004i-0900000000-973fc871534b19242cc8	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Liothyronine LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative-QTOF	splash10-004i-0900000000-ac3c4a198bb017dc7ccc	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Liothyronine LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive-QTOF	splash10-0udi-0000009000-2770ece749a9fa1042f4	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Liothyronine LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive-QTOF	splash10-0udi-0000009000-881174c66da97022d645	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Liothyronine LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive-QTOF	splash10-0a4i-0000019000-6f798ae76702a3053339	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Liothyronine LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive-QTOF	splash10-0a4i-0000219000-d2ca9f0cc3c1b47176b5	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Liothyronine LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive-QTOF	splash10-056r-0021915000-6f3810619f383bce651a	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Liothyronine LC-ESI-QQ , negative-QTOF	splash10-0udi-0000009000-f932659d1e6d8a622985	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Liothyronine LC-ESI-QQ , negative-QTOF	splash10-0udi-0000009000-6506a7a71dab928abfb0	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Liothyronine LC-ESI-QQ , negative-QTOF	splash10-0fc0-0700119000-1df6db0e3031eb2739fa	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Liothyronine LC-ESI-QQ , negative-QTOF	splash10-004i-0900000000-973fc871534b19242cc8	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Liothyronine LC-ESI-QQ , negative-QTOF	splash10-004i-0900000000-ac3c4a198bb017dc7ccc	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Liothyronine LC-ESI-QQ , positive-QTOF	splash10-0udi-0000009000-2770ece749a9fa1042f4	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Liothyronine 10V, Positive-QTOF	splash10-0pb9-0000009000-4d60e144164273111464	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Liothyronine 20V, Positive-QTOF	splash10-0a4i-0000149000-87babecf610c68223da5	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Liothyronine 40V, Positive-QTOF	splash10-016r-0039010000-b57f6dd23e6456cf7c1e	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Liothyronine 10V, Negative-QTOF	splash10-0002-0010009000-50e441d89395debe176b	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Liothyronine 20V, Negative-QTOF	splash10-001j-0050139000-a259e39ad1204b60b373	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Liothyronine 40V, Negative-QTOF	splash10-00e9-9262431000-bcc1f7554c4e309cef17	2017-07-26	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Experimental 1D NMR	¹H NMR Spectrum (1D, 600 MHz, 100%_DMSO, experimental)	2012-12-04	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, 100%_DMSO, experimental)	2012-12-05	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Membrane (predicted from logP)

Biospecimen Locations

Blood
Saliva
Urine

Tissue Locations

Adipose Tissue
Adrenal Gland
Epidermis
Fibroblasts
Intestine
Neuron
Placenta
Platelet
Skeletal Muscle
Testis
Thyroid Gland

Pathways

Name	SMPDB/PathBank	KEGG
Tyrosine metabolism	Not Available
Thyroid hormone synthesis		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.0029 +/- 0.00019 uM	Children (1-13 years old)	Both	Normal	10731506	details
Blood	Detected and Quantified	0.002 +/- 0.0006 uM	Adolescent (13-18 years old)	Female	Normal	10197568	details
Blood	Detected and Quantified	0.000013 - 0.000028 uM	Adult (>18 years old)	Both	Normal	K&S Clinical...	details
Blood	Detected and Quantified	0.0000038 - 0.0000060 uM	Adult (>18 years old)	Both	Normal	K&S Clinical...	details
Blood	Detected and Quantified	0.0000031-0.0000077 uM	Adult (>18 years old)	Not Specified	Normal	7477119	details
Saliva	Detected and Quantified	0.0 - 1.0 uM	Adult (>18 years old)	Both	Normal	15179829	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.0011 +/- 0.00024 uM	Children (1-13 years old)	Both	Malnutrition (type kwashiorkor and marasmus)	10731506	details
Blood	Detected and Quantified	0.0014 +/- 0.0004 uM	Adolescent (13-18 years old)	Female	Anorexia nervosa	10197568	details
Blood	Detected and Quantified	0.00169 uM	Adult (>18 years old)	Female	Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency	7951484	details
Blood	Detected and Quantified	0.0000041 uM	Adult (>18 years old)	Female	Proprotein Convertase 1/3 Deficiency	7477119	details
Urine	Detected and Quantified	0.00075 +/- 0.00033 umol/mmol creatinine	Adult (>18 years old)	Both	Hyperthyroidism	7256725	details
Urine	Detected and Quantified	0.000014 +/- 0.000015 umol/mmol creatinine	Adult (>18 years old)	Both	Hypothyroidism	7256725	details

Predicted Concentrations

Biospecimen	Value	Original age	Original sex	Original condition	Comments
Blood	0.000 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities

Associated Disorders and Diseases

Disease References

Anorexia nervosa
Capo-chichi CD, Gueant JL, Lefebvre E, Bennani N, Lorentz E, Vidailhet C, Vidailhet M: Riboflavin and riboflavin-derived cofactors in adolescent girls with anorexia nervosa. Am J Clin Nutr. 1999 Apr;69(4):672-8. [PubMed:10197568 ]
Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency
Hattori N, Ishihara T, Moridera K, Hino M, Ikekubo K, Kurahachi H: A case of late-onset congenital adrenal hyperplasia due to partial 3 beta-hydroxysteroid dehydrogenase deficiency. Endocr J. 1993 Feb;40(1):107-9. [PubMed:7951484 ]
Proprotein Convertase 1/3 Deficiency
O'Rahilly S, Gray H, Humphreys PJ, Krook A, Polonsky KS, White A, Gibson S, Taylor K, Carr C: Brief report: impaired processing of prohormones associated with abnormalities of glucose homeostasis and adrenal function. N Engl J Med. 1995 Nov 23;333(21):1386-90. doi: 10.1056/NEJM199511233332104. [PubMed:7477119 ]
Hyperthyroidism
Yoshida K, Sakurada T, Kaise N, Yamamoto M, Kaise K, Saito S, Yoshinaga K: Measurement of triiodothyronine in urine. Tohoku J Exp Med. 1980 Dec;132(4):389-95. [PubMed:7256725 ]
Hypothyroidism
Yoshida K, Sakurada T, Kaise N, Yamamoto M, Kaise K, Saito S, Yoshinaga K: Measurement of triiodothyronine in urine. Tohoku J Exp Med. 1980 Dec;132(4):389-95. [PubMed:7256725 ]

Associated OMIM IDs

606788 (Anorexia nervosa)
201810 (Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency)
600955 (Proprotein Convertase 1/3 Deficiency)

External Links

DrugBank ID

DB00279

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C02465

BioCyc ID

CPD-10813

BiGG ID

Not Available

Wikipedia Link

Triiodothyronine

METLIN ID

Not Available

PubChem Compound

5920

PDB ID

Not Available

ChEBI ID

18258

Food Biomarker Ontology

Not Available

VMH ID

TRIODTHY

MarkerDB ID

MDB00000128

Good Scents ID

Not Available

References

Synthesis Reference

Salamonczyk, Grzegorz M.; Oza, Vibha B.; Sih, Charles J. A concise synthesis of thyroxine (T4) and 3,5,3'-triiodo-L-thyronine (T3). Tetrahedron Letters (1997), 38(40), 6965-69

Material Safety Data Sheet (MSDS)

Not Available

General References

Schwartz CE, May MM, Carpenter NJ, Rogers RC, Martin J, Bialer MG, Ward J, Sanabria J, Marsa S, Lewis JA, Echeverri R, Lubs HA, Voeller K, Simensen RJ, Stevenson RE: Allan-Herndon-Dudley syndrome and the monocarboxylate transporter 8 (MCT8) gene. Am J Hum Genet. 2005 Jul;77(1):41-53. Epub 2005 May 11. [PubMed:15889350 ]
Gil'miiarova FN, Pervova IuV, Radomskaia VM, Gergel' NI, Tarasova SV: [Levels of unified metabolites and thyroid hormones in blood and oral fluid of children with minimal brain dysfunction]. Biomed Khim. 2004 Mar-Apr;50(2):204-10. [PubMed:15179829 ]
Escobar-Morreale HF, Botella-Carretero JI, Gomez-Bueno M, Galan JM, Barrios V, Sancho J: Thyroid hormone replacement therapy in primary hypothyroidism: a randomized trial comparing L-thyroxine plus liothyronine with L-thyroxine alone. Ann Intern Med. 2005 Mar 15;142(6):412-24. [PubMed:15767619 ]
Stalenheim EG: Long-term validity of biological markers of psychopathy and criminal recidivism: follow-up 6-8 years after forensic psychiatric investigation. Psychiatry Res. 2004 Jan 1;121(3):281-91. [PubMed:14675747 ]
Zimmermann-Belsing T, Dreyer M, Holst JJ, Feldt-Rasmussen U: The relationship between the serum leptin concentrations of thyrotoxic patients during treatment and their total fat mass is different from that of normal subjects. Clin Endocrinol (Oxf). 1998 Nov;49(5):589-95. [PubMed:10197073 ]
Holt PJ: In vitro responses of the epidermis to triiodothyronine. J Invest Dermatol. 1978 Sep;71(3):202-4. [PubMed:690484 ]
Mizuma H, Murakami M, Mori M: Thyroid hormone activation in human vascular smooth muscle cells: expression of type II iodothyronine deiodinase. Circ Res. 2001 Feb 16;88(3):313-8. [PubMed:11179199 ]
Himms-Hagen J: Brown adipose tissue thermogenesis: interdisciplinary studies. FASEB J. 1990 Aug;4(11):2890-8. [PubMed:2199286 ]
Gledhill RF, Dessein PH, Van der Merwe CA: Treatment of Raynaud's phenomenon with triiodothyronine corrects co-existent autonomic dysfunction: preliminary findings. Postgrad Med J. 1992 Apr;68(798):263-7. [PubMed:1409189 ]
Kassem M, Brixen K, Mosekilde L, Blum WF, Flyvbjerg A: Effects of growth hormone treatment on serum levels of insulin-like growth factors (IGFs) and IGF binding proteins 1-4 in postmenopausal women. Clin Endocrinol (Oxf). 1998 Dec;49(6):747-56. [PubMed:10209562 ]
Llewellyn L, Ramsurn VP, Wigham T, Sweeney GE, Power DM: Cloning, characterisation and expression of the apolipoprotein A-I gene in the sea bream (Sparus aurata). Biochim Biophys Acta. 1998 Nov 8;1442(2-3):399-404. [PubMed:9804999 ]
Dutkiewicz S, Witeska A, Nauman A: The deiodination of thyroxine to triiodothyronine in the testes of patients with prostate cancer. Int Urol Nephrol. 1995;27(1):81-5. [PubMed:7615374 ]
Rosenbaum M, Goldsmith R, Bloomfield D, Magnano A, Weimer L, Heymsfield S, Gallagher D, Mayer L, Murphy E, Leibel RL: Low-dose leptin reverses skeletal muscle, autonomic, and neuroendocrine adaptations to maintenance of reduced weight. J Clin Invest. 2005 Dec;115(12):3579-86. [PubMed:16322796 ]
Urcelay E, Jareno MA, Menaya J, Parrilla R, Ayuso MS, Martin-Requero A: Cloning and functional characterization of the 5' regulatory region of the human mitochondrial glycerol-3-phosphate dehydrogenase gene. Lack of 3,5,3'-triiodothyronine responsiveness in adipose tissue. Eur J Biochem. 2000 Dec;267(24):7209-17. [PubMed:11106433 ]
Lebon V, Dufour S, Petersen KF, Ren J, Jucker BM, Slezak LA, Cline GW, Rothman DL, Shulman GI: Effect of triiodothyronine on mitochondrial energy coupling in human skeletal muscle. J Clin Invest. 2001 Sep;108(5):733-7. [PubMed:11544279 ]
Iwao H, Abe Y: [Expression of the renin and angiotensinogen genes]. Nihon Yakurigaku Zasshi. 1991 Jan;97(1):1-11. [PubMed:2045011 ]
Calvo R, Obregon MJ, Ruiz de Ona C, Escobar del Rey F, Morreale de Escobar G: Congenital hypothyroidism, as studied in rats. Crucial role of maternal thyroxine but not of 3,5,3'-triiodothyronine in the protection of the fetal brain. J Clin Invest. 1990 Sep;86(3):889-99. [PubMed:2394838 ]
Haas MJ, Fishman M, Mreyoud A, Mooradian AD: Thyroid hormone responsive protein (THRP) mediates thyroid hormone-induced cytotoxicity in primary neuronal cultures. Exp Brain Res. 2005 Jan;160(4):424-32. Epub 2004 Oct 15. [PubMed:15490139 ]

Enzymes

Enzyme Details

1. Thyroid peroxidase

General function:: Involved in calcium ion binding
Specific function:: Iodination and coupling of the hormonogenic tyrosines in thyroglobulin to yield the thyroid hormones T(3) and T(4).
Gene Name:: TPO
Uniprot ID:: P07202
Molecular weight:: 102961.63

Reactions

Iodotyrosine + 3,5-Diiodo-L-tyrosine + Hydrogen peroxide → Liothyronine + 2-Aminoacrylic acid + Water	details

Enzyme Details

2. Type I iodothyronine deiodinase

General function:: Involved in thyroxine 5'-deiodinase activity
Specific function:: Responsible for the deiodination of T4 (3,5,3',5'-tetraiodothyronine) into T3 (3,5,3'-triiodothyronine) and of T3 into T2 (3,3'-diiodothyronine). Plays a role in providing a source of plasma T3 by deiodination of T4 in peripheral tissues such as liver and kidney.
Gene Name:: DIO1
Uniprot ID:: P49895
Molecular weight:: 28924.21

Reactions

Liothyronine + I(-) + A + Hydrogen Ion → Thyroxine + AH(2)	details

Enzyme Details

3. Type II iodothyronine deiodinase

General function:: Involved in thyroxine 5'-deiodinase activity
Specific function:: Responsible for the deiodination of T4 (3,5,3',5'-tetraiodothyronine) into T3 (3,5,3'-triiodothyronine). Essential for providing the brain with appropriate levels of T3 during the critical period of development.
Gene Name:: DIO2
Uniprot ID:: Q92813
Molecular weight:: 30551.48

Reactions

Liothyronine + I(-) + A + Hydrogen Ion → Thyroxine + AH(2)	details

Enzyme Details

4. Transthyretin

General function:: Involved in hormone activity
Specific function:: Thyroid hormone-binding protein. Probably transports thyroxine from the bloodstream to the brain
Gene Name:: TTR
Uniprot ID:: P02766
Molecular weight:: 15886.9

Enzyme Details

5. Serum albumin

General function:: Involved in transport
Specific function:: Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloidal osmotic pressure of blood. Major zinc transporter in plasma, typically binds about 80% of all plasma zinc
Gene Name:: ALB
Uniprot ID:: P02768
Molecular weight:: 69365.9

Enzyme Details

6. Thyroxine-binding globulin

General function:: Involved in serine-type endopeptidase inhibitor activity
Specific function:: Major thyroid hormone transport protein in serum
Gene Name:: SERPINA7
Uniprot ID:: P05543
Molecular weight:: 46324.1

Enzyme Details

7. Thyroid hormone receptor beta

General function:: Involved in sequence-specific DNA binding transcription factor activity
Specific function:: High affinity receptor for triiodothyronine
Gene Name:: THRB
Uniprot ID:: P10828
Molecular weight:: 52787.2

Enzyme Details

8. Type III iodothyronine deiodinase

General function:: Involved in thyroxine 5'-deiodinase activity
Specific function:: Responsible for the deiodination of T4 (3,5,3',5'-tetraiodothyronine) into RT3 (3,3',5'-triiodothyronine) and of T3 (3,5,3'-triiodothyronine) into T2 (3,3'-diiodothyronine). RT3 and T2 are inactive metabolites. May play a role in preventing premature exposure of developing fetal tissues to adult levels of thyroid hormones. Can regulate circulating fetal thyroid hormone concentrations throughout gestation. Essential role for regulation of thyroid hormone inactivation during embryological development.
Gene Name:: DIO3
Uniprot ID:: P55073
Molecular weight:: 33947.175

Reactions

Liothyronine + I(-) + A + Hydrogen Ion → Thyroxine + AH(2)	details

Enzyme Details

9. Thyroid hormone receptor alpha

General function:: Involved in sequence-specific DNA binding transcription factor activity
Specific function:: Nuclear hormone receptor. High affinity receptor for triiodothyronine
Gene Name:: THRA
Uniprot ID:: P10827
Molecular weight:: 54815.1

Showing metabocard for Liothyronine (HMDB0000265)

MOL for HMDB0000265 (Liothyronine)

3D MOL for HMDB0000265 (Liothyronine)

3D SDF for HMDB0000265 (Liothyronine)

3D-SDF for HMDB0000265 (Liothyronine)

PDB for HMDB0000265 (Liothyronine)

3D PDB for HMDB0000265 (Liothyronine)

SMILES for HMDB0000265 (Liothyronine)

INCHI for HMDB0000265 (Liothyronine)

Structure for HMDB0000265 (Liothyronine)

3D Structure for HMDB0000265 (Liothyronine)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

Reactions

Reactions

Reactions

Reactions